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Making midnight memories! Harry Styles rang in his 23rd birthday on Wednesday, February 1, with a celebration attended by a bevy of super-famous friends. The former One Direction singer — wearing his signature open button-down shirt, white tee, jeans and boots — celebrated at Cafe Habana in Malibu with roughly 30 pals, includingCindy Crawford, Rande Gerber, their daughter, Kaia Gerber, and even fellow Brit Adele. Cuba Gooding Jr., who was at the restaurant for karaoke night with his own pals, also stopped by to wish the singer a happy birthday.

As the crew sat in a private section of the eatery, the birthday boy and restaurateur Rande, 54, downed shots of Casamigos Tequila while Adele sipped margaritas. An eyewitness tells Us Weekly that the “Hello” singer, 28, later stood on a couch in the back of the space to watch others perform karaoke. (Sadly, the 10-time Grammy winner never got behind the mic herself!) Crawford, 50, and her 15-year-old daughter also enjoyed the tunes, and danced to one singer's rendition of Prince’s “Kiss.” Styles “was super excited” to hear the late legend’s song, adds the eyewitness, noting that “he was smiling during the entire song and threw a fist pump in the air at the chorus.”

Crawford and her young model daughter stuck by Styles' side for most of the evening. "They were very friendly with him,” says the eyewitness. "Harry seemed to be very interested in talking to Kaia — not in a flirtatious way, but as if they were really good friends."

The man of the hour "looked like he was having a really good time with his friends,” adds the observer.

It seems that 23 will be a big year for the pop crooner. In June 2016, Styles officially went solo after signing a recording contract with Columbia Records. Though no release date for an album has been announced, four songs by Styles were registered with the American Society of Composers, Authors and Publishers in late 2015.